HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-bromo-N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-butanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-Bromobutyryl chloride | HCID 70225 | — |
| Reactant | 4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline | HCID 67145657 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-bromo-N-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]-butanamide | HCID 86677217 | — |
Reaction Steps
To a solution of 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline (intermediate 39; 0.75 g, 2.48 mmol) in tetrahydrofuran (20 mL) and triethylamine (0.38 mL, 2.73 mmol) was added under nitrogen atmosphere at 0° C. 4-bromobutanoyl chloride (0.32 mL, 2.76 mmol). The mixture was stirred for half an hour. Ethyl acetate was added to the mixture and the organic layer was washed with bicarbonate and brine, dried and the solvent was removed under reduced pressure. The title compound was obtained (97%) and it was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09315463B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-191337b7391a43d0825edefa616fc92a |
| Source note | uspto-grants-2016_04 |